


Double Trouble

by thealexiad



Category: How to Get Away with Murder, Shameless (US)
Genre: Crossover, Double Date, Fluff, M/M, abuse mention, prompt
Language: English
Status: Completed
Published: 2014-11-06
Updated: 2014-11-06
Packaged: 2018-02-24 08:07:18
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,952
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2574290
Author URL: https://archiveofourown.org/users/thealexiad/pseuds/thealexiad
Summary: <blockquote class="userstuff">
              <p>So, after getting an anon prompt (about a month ago - sorry anon!) asking what a double date with Ian & Mickey and Connor & Oliver would be like, I decided to go a bit overboard and write a whole fic. This is the result.</p>
            </blockquote>





	Double Trouble

Mickey didn’t know how he had let Ian talk him into this. He knew that Ian had slowly drifted apart from the friends he’d made working at the club once he’d finally quit his job there, and he knew that Ian had been talking for months now about how they really do have to go out and meet other gay couples. In a way Mickey could certainly empathize with him; more and more he’d been finding it tiring to operate in the world surrounded by straight people. At least he supposed that it might be nice having someone in addition Ian who he could talk to about stuff – as much as he loved Ian, he’d also appreciate being able to hear from a different perspective once in a while.

Though Mickey was still happy to go to gay bars and clubs with Ian on occasion, he still didn’t feel totally comfortable there – if his usual discomfort around crowds wasn’t enough, his memories of Ian’s exploitation made going to Boystown a less than enjoyable experience for him, and Ian could tell. Even when they did go out together their nights usually consisted of Ian standing with Mickey in a corner, sodas in hand (Ian had decided to stop drinking alcohol once he’d gone on his medication and Mickey had unilaterally come to an understanding that he would stop as well). A few patrons who had already known Ian would come over and talk for a few minutes, but when they tried to engage Mickey he would normally scarcely let out more than a grunt or two, maybe occasionally forming a complete sentence. As interesting as he was sure symbolic interactionism in hustler-client relations was, he was a few miles north of his comfort zone.

A few weeks ago however Ian brought up that he’d made a new friend at work who he endorsed as a “really cool guy!” Mickey hadn’t thought much of it; they’d fallen into a rather predictable routine now, and though Mickey was listening he’d fallen into the habit of filing most of the information away as he received it. If something was wrong or if Ian had something really important to say Mickey would pick up on it, but somehow the news on this new friend had slipped by him.

So when Ian had told him on Tuesday that “I told Oliver we’d go on the double date this Thursday!” Mickey nearly spit out his hot chocolate.

“Double date? The fuck are you talkin’ about?”

“I’m talking about the…uh…double date?”

Mickey’s eyebrows had collided with his hairline.

“God Mick, the double date? With Oliver and his boyfriend?”

“Oliver?”

“Mickey, are you fucking seri-”

Mickey finally found the right filing cabinet in his Milkovich mind. “Ah right, Oliver.”

This hadn’t seemed enough to totally placate Ian, but it had been enough to at least get him back on topic. “Yeah, so we’re going to meet him and his boyfriend downtown Thursday night.”

 _Boyfriend? Huh._ Mickey had been somewhat intrigued, but not intrigued enough to override his normal verbal reflexes. “Don’t really have a choice, do I?”

If Ian had still been a little annoyed about Mickey’s lack of listening skills, he hid it behind his classic “oh Mickey!” smile. “That’s right! Gotta pay your dues!” And with that the ginger pixie had up and bounced away, floating on bliss, no doubt to magically resurrect some garden somewhere. Or maybe to take out the trash; it was one of the two, Mickey just wasn’t sure sometimes.

Now it was Thursday night, and Mickey was standing with Ian outside some really modern-looking, haute-couture, hoity-toity bar in his best clothes, a fact that he sure as hell hoped none of these high-class peacocks strutting around him were aware of.

* * *

 

Connor didn’t know how he had let Oliver talk him into this. He knew that Oliver was missing all of his work friends that he’d had to leave behind in Philadelphia, and he knew that Oliver had been talking for the entire two months they’d lived in Chicago so far about the possibility of actually making some gay friends here. Connor certainly couldn’t blame him; it was after all because of Connor that they had moved here. Upon his graduation from Middleton, Connor’s job search had turned up nothing of real value in Philadelphia, but within a month or so a great opportunity came up in Chicago. By now he and Oliver had been together for two and a half years, and they’d lived together for the entirety of Connor’s time as a 3L. About a week after he had received the offer from the Chicago firm, he finally pulled himself together enough to bring it up to Oliver

Of course he was not about to demand that Oliver move with him, but at the same time the prospect of a long-distance relationship terrified him. Luckily for him, Oliver revealed that he already had multiple offers in Chicago from companies trying to poach him. Connor had muttered something about how great the job market is for “mathy guys like you” and how it “just isn’t fair,” but in the end his happiness over the fact that he wouldn’t have to leave Oliver was enough cut through his snark, and there they shared one of the most passionate kisses that Connor could remember.

They had spent most of their first couple months in Chicago just exploring the city together, hanging out in their nice new apartment together, and generally not being apart whenever they both had time off. Sure, they both had made some friends at work who they might occasionally grab a drink with right after getting out of the office for the day, but even then this would just mean that the one going out would get home an hour or two late, and the two of them would end up watching Netflix or reading in bed together - along with a round or two of sex, of course.

The past few weeks had been very busy for both of them however, and it seemed like the few nights that Connor didn’t have to work late in the office on his first really tough case that he was taking himself were the nights that Oliver had to stay late in his office working on an upgrade for his company’s computer network.

Finally on Wednesday night neither Connor nor Oliver had work obligations, and all seemed well; but as Connor was basking in the afterglow of their first after-work fuck in what seemed like decades he had noticed a look of shocked realization come to Oliver’s face. Connor had felt his heart drop even as his mind had been racing to determine what was wrong with Oliver.

Fortunately, before Connor could think of anything especially dark, Oliver spoke. “Oh…oh crap. How’d I forget to tell you until now-”

“Forget to tell me what, Oliver?”

“Ugh this is just like me to be so forgetful, but over the weekends I just try to shut out anything work-related. Not that this is necessarily work-related, but-”

Connor lost his patience. He placed his hands on the sides of Oliver’s head and turned his face towards his own. “Oliver, what is it?”

Oliver quickly grabbed Connor’s forearms and pulled his hands off of his face before leaning in for a quick smooch. “Well, you see, I told a guy at work that we’d go out on a double date with our boyfriends.”

“There’s a-? Well alright, when is it?”

“Tomorrow.”

“Aww, but tonight is the first night we’ve had to ourselves in weeks…”

“…Except for the weekends.”

“Weekends don’t count though.”

“God you’re needy.” Oliver had lain down. “Double date. Tomorrow.”

Connor had let out something between a whimper and a sigh, but he knew that when Oliver was this determined there was nothing stopping him. He had lain down himself and opened to the next page of _The Velvet Rage_. He had never been on a double date before, let alone with another gay couple. Hell, he didn’t even know the other pair’s names. He had looked to Oliver to ask, but the other man was already fast asleep.

Now it was Thursday night, and the two of them were navigating the El, as Oliver hadn’t thought to plot out the route beforehand. Oliver was on the phone with Ian, the receptionist at Oliver’s company whom he had befriended, desperately trying to get his bearings. Connor leaned his stubbled face against the freezing window, dreaming of Netflix.

* * *

 

Mickey was keeping track of the amount of time that they’d been waiting for these two jokers, Oliver and Conrad or whatever their names were. Fifteen minutes so far. Ian had spent seven of those minutes on the phone with Oliver, giving him directions to the restaurant. This seemed fairly silly to Mickey, since these rich yuppies should really know this part of town better than a couple of South Siders. Just as Mickey was about to go on his third tirade to Ian about how rich people were never on time, he saw a two men round the corner, and by the way they were comfortably walking so close to each other Mickey knew it was them.

The one on the left was the taller of the two by no more than an inch, and judging by his glasses and the somewhat nerdy vibe he exuded Mickey assumed that he was the guy who worked in IT at Ian’s company. His face seemed kind and genuine, and the smile he was already wearing widened as he saw Ian at the table.

The one on the right was also had an expression that one could describe as a smile, but it would really be more accurate to call it a smirk. It seemed to be stuck on his face however, and as Mickey looked at his brown eyes he could see them giving the room a quick scan, flashing from table to table. Both men were well-dressed, but the one with the smirk and the gelled hair definitely put more thought into his fashion choices.

As the IT guy, Oliver, arrived at the table, Ian stood up and reached his hand out to meet Oliver’s handshake.

“Nice to see you Ian!”

“Same to you, Oliver!”

Oliver’s boyfriend hung back while Mickey himself didn’t make a move, and it took Oliver and Ian a few awkward seconds to realize that they should probably introduce their respective grumps. They both tried to start at the same time with “So, this is-oh!”

Ian was the first to regroup. “This is Mickey. Mickey, this is Oliver and-”

Hair-gel spoke before Oliver could get a word in. “Connor. Connor Walsh.” He brusquely shook Ian’s hand before going to the sitting Mickey, who was trying to ignore the fact that Connor thought it necessary to include his last name, and offering his palm out.

Mickey tentatively grabbed Connor’s hand for a second, giving a sort of half-handshake, before quickly withdrawing and leaning a bit into Ian. Oliver and Connor took their seats on the other side of the table, opening their menus to look over a selection which Mickey had already memorized in the time he and Ian had spent waiting for them.

The table was silent for a couple minutes, aside from the two couples whispering among themselves about various mundane matters as they were wont to do. Ian finally broke down the barrier of silence that had emerged across the table.

“So, Connor, what do you do?”

Connor continued to read his menu for a few seconds before he evidently noticed Oliver open his mouth in his peripheral vision, and subsequently answered the question so he wouldn’t have to have his boyfriend speaking for him.

“I’m a lawyer,” Connor answered brusquely before training is eyes back on the menu.

Ian was not one to concede defeat so easily though, and Mickey couldn’t help but smirk as the redhead pressed forward with another question.

“What kind of lawyer?”

Connor raised an eyebrow as he looked back at Ian over the menu. “I work in…uh…employment law.”

“Employment law?”

“Yeah my firm, we, uh, we handle cases of employment discrimination against MOGII – you might call them LGBT – people.”

“That’s pretty cool!”

Connor made a smile that was somewhat more genuine than before. “Yeah, I think so too. I could have gone into a private defense firm but Ollie here,” he patted his bespectacled boyfriend on the shoulder, “convinced me to, what did you say, ‘do the right thing’?” Connor tilted his head sideways as he looked with admiration at Oliver.

Oliver smiled back. “Yeah, something like that.”

Connor leaned in and placed his forehead on Oliver’s before giving him a quick peck on the lips. Right then the waiter came back to the table, asking for their orders…

* * *

 

…Once they had finished ordering, the two couples turned back to face one another. Well, Connor was still staring at Oliver with his hand on Oliver’s thigh – such casual and continuous contact had become second nature to him by now. He was snapped out of his trance when Oliver spoke.

“So, Mickey, what do you do?”

The blue-eyed man shifted in his seat and rapped his right knuckles on the table, which Connor noticed had “FUCK” tattooed on them. This elicited an eyebrow-raise from Connor, who couldn’t help but speculate where the apparently well-put together young man had gotten such a marking.

“I’m, ah, a mechanic.”

Oliver nodded his head, “Sounds like a good job. You like it?”

Mickey shrugged his shoulders. “It pays the bills.”

Ian elbowed him in the side. “Hey, I help pay the bills too!”

The shorter man raised his eyebrows and turned to face his red-haired boyfriend. “Yeah well we’re both helping to pay the bills for your courses, asshole.” His blue eyes dove into Ian’s green eyes for an instant before he leaned in to exchange a small kiss with his boyfriend. The tough-looking young man’s voice went soft as he leaned into the taller man’s chest. “I love you, man, and I’m so proud of you.”

Connor felt a pang of envy in his stomach; as close as he and Oliver were at this point, there was something between Ian and Mickey that he couldn’t describe. It was almost as if they shared some deep, heavy pain. As if they each had their own burdens that they couldn’t carry without the other there. As much as he loved Oliver and as much as he knew Oliver loved him, there was something different about the way Ian and Mickey looked into each other’s eyes. Even though they were younger than Connor and Oliver, they looked as if they had been through far more than their youth warranted.

Perhaps, Connor mused, such pain was not something to be envious of. As Mickey ran his left hand over Ian’s arm, Connor also noticed a set of tattoos spelling out “U-UP”, apparently to match the “FUCK” on the right hand. Connor’s curiosity and the investigative spirit which he’d developed under Professor Keating got the better of him.

“Where’d you get those tattoos?”

Mickey immediately swiveled his face from Ian to Connor.

“The f-…excuse me?”

The lawyer got the sense that he might be prying a bit too deep, but he took Mickey’s reaction as a sort of challenge.

“The tattoos? Where are they from?”

Mickey’s tattooed knuckles turned white as he clenched his fist at the question. “That’s none of your f-”

Ian moved just in time to avert disaster. “Mickey had a…err…rough home life growing up. Family problems.”

Mickey seemed satisfied by the answer his boyfriend had offered on his behalf, and relaxed hand a bit.

Connor thought to his own upbringing with his cold, distant parents. “I can sympathize.”

This seemed to set Mickey off all over again. “Oh, you can sympathize can you? Your dad held you down while calling you a ‘pussy’ when you were fourteen? Your dad had one of your brothers stick ink into your skin, telling you that this would make you a ‘real man’? Please, I know enough about people like you to-”

“What the hell do you know about me? My dad barely spoke ten words to me when I was fourteen! And then the year after they sent me off to boarding school and-”

“Oh, boarding school! Yeah you must’ve had it real tough up there in Vermont-”

Connor rolled his eyes. “It was New Hampshire, actually, and I-”

“I bet your parents didn’t even care that you were gay, I bet they-”

“My parents barely cared about anything at all, so of course they didn’t care!”

“Yeah so I bet your dad didn’t try to beat you to death when you came out to him, huh?” Mickey was shaking by this point, and Ian gently placed his hand over his boyfriend’s in an attempt to calm him.

Connor was for once at a loss for words. He tried to open his mouth but his brain couldn’t formulate the syllables. “I-I-I’m so fucking – I’m so fucking sorry, man. I didn’t know-”

“How the fuck could you have known? You ever try thinking that maybe some people do actually have it worse than you? Rick fucks like you who think you can just – that you can just-” Mickey pounded his fist on the table.

Ian rubbed his shoulder. “I think maybe we should take a step outside.” He turned to Oliver. “We’ll be back in a few.”

Oliver nodded. “Alright.”

Once the younger couple was gone, Connor buried his face in his hands. “What the fuck just happened?”

Oliver’s tone was somewhat exasperated. “Connor you really need to learn when to stop.”

Connor thought back to before he and Michaela had become friends, back when he couldn’t stop harassing her about Aiden. “Why are you always right?”

Oliver chuckled. “It’s not as hard as you might think with you around.”

* * *

 

Mickey paced around outside, each of his heavy breaths turning to steam in the cold night air. Ian was standing with his back against the side of the building, apparently waiting for Mickey to calm down.

“Can we just fucking go home? These two are just like-”

“Just like who, Mick?”

“Like those rich fucks at the club, those rich guys who thought that they owned you – hell, they thought they owned me more than a few times. We don’t fucking need to deal with those kinds of people again, Ian!”

Ian sighed. “Mickey, Oliver’s not like that, and Connor’s not either. They might not look like it but they’ve been through some shit together – a lot of shit. Sure, maybe not the same shit as us, but from talking to Oliver at work it really sounds like you and Connor might have more in common than you might think. They’re not bad people, not like those-” Ian waved his hand, still not fully comfortable verbalizing his experiences working at the club.

“Really though? Like me and hair-gel over there could have anything in common? Guy’s a fuckin’ asshole.”

Ian grinned wide as ever. “Exactly.”

Mickey couldn’t help but smile as well. “Fuck you, man.”

“That a challenge?”

That got a laugh out of Mickey. “God, Ian, that’s so fucking old. Is it really that hard to think up a new pun?”

“It still makes you laugh, doesn’t it?”

Mickey went up to Ian and, going on his tip-toes a bit, gave him a kiss while holding him tight and close in the freezing winter air. It really was amazing, Mickey thought, that he was here, on a public sidewalk on a crowded street, kissing his boyfriend. Maybe it’d be worth it to take another chance, especially if it was for Ian.

“Alright, alright let’s go back in.”

By the time they got back to their table their meals were already on the table. Ian sat down without a word and ravenously attacked his food, while Mickey sat at his place across from Connor.

“So, uh, how’s the food?”

Connor looked up, apparently surprised that Mickey was talking to him at all. “It’s, uh, it’s pretty good – really good! Yeah, it’s great!”

Mickey smiled, in part because just his voice seemed to be enough to make Connor uncomfortable, and as he dug in to his meal he found that Connor was certainly not wrong, at least in this case.

* * *

 

Connor looked around the table to find that he was the last one still working on his food, even though he had started before the two Chicago boys. As he finished up his last bites, Ian posed a question to him and Oliver.

“So how’d you guys meet?”

Connor shot a look at Oliver to find that Oliver was looking right back at him. He could tell from the look Oliver was giving him that he was expected to be the one to answer this question. Which was fair enough; there was certainly more than a little explaining to do.

“Well, you see, I was in law school. I was working for this lawyer in Philadelphia – well no, at the time I was in a competition to get to work for her. Anyways, one of the other students in the class had made a really good impression on Professor Keating – that’s the lawyer, she was also my professor – and I knew I had to one-up her, because this woman – the other student, Michaela – she knew what she was doing.”

Ian leaned in over his plate, obviously intrigued. “So, what’d you do?”

Connor scratched the back of his head. “I decided to go for a more…high risk, high reward strategy.”

Mickey raised his eyebrows across the table. Connor was somewhat reluctant to go on, because if Mickey hadn’t already judged him earlier he certainly would now. A sideways glance at Oliver, who was looking at him just as intently as the other two, confirmed that he had to carry on however.

“So I, uh, went to a bar near the company – okay the case was about a woman at this company who tried to kill her boss slash lover – with an asprin – he was allergic to asprin – but anyways, I went to this bar in the same building at the company, and I saw this cute guy looking at me, who I assumed must have been an employee” – Oliver smiled when he said cute – “so I went over to him and asked him if I could buy him a drink.”

Mickey chimed in, if only perhaps to appear interested. “What drink did he ask for?”

Connor and Oliver replied at the same time “Maker’s Manhattan, two cherries.” Connor looked at Oliver who was looking back at him, and they both laughed, Connor leaning into Oliver’s chest to stabilize himself. Once he regained his faculties, he continued.

“And I really didn’t know what drink to get myself, so I got the same one. But anyways, I flirted with him a bit-”

Oliver chuckled “Just say the word and we can start making out.”

Ian and Mickey both widened their eyes at Connor, who leaned back and put his hands up. “Yeah, I was a bit forward back then. But it worked, didn’t it? Anyways, we talked a bit, and I found out he worked in the IT department of the company. So, I, uh…”

Connor looked somewhat sheepishly at Oliver, who nodded.

“I asked him to get some emails from the company for me - for the case. I really did like him though, and we hooked up for the first time later that night. But yeah, we only met because I was committing corporate espionage. Not the best start, but I think we’ve made it work.”

Oliver placed a hand on his shoulder and rubbed it. “Oh, you think so?”

Connor reached across his body to place his own hand on Oliver’s. “Yeah I do.” He gave Oliver another kiss.

Ian laughed “We didn’t exactly get off to the smoothest start either, huh, Mickey?”

“You could say that.”

* * *

 

Mickey braced himself to hear Ian’s ten-thousandth retelling of the first time they got together.

“It all started when…well Mickey used to be something of a problem child.”

Connor snickered “Never would’ve guessed – ow!” He rubbed his side where Oliver had landed a well-placed elbow.

Mickey allowed himself to smirk. “Oh you don’t know the half of it – I had the whole neighborhood in my grip.”

Ian nudged up against him. “Well, I wouldn’t say that, Mick.”

“Who was it that literally walked into that store, took what he needed, and walked out in front of the manager without paying a cent?”

“Whatever Mickey – anyways, well yeah, he was stealing stuff from the store, and the owner-”

“Let’s not talk about him-”

“…Yeah…but yeah the owner had a gun for protecting the store, which he never used-”

“Oh, he used it alright. I can show the fuckin’-” Now it was Connor and Oliver’s turn to widen their eyes in surprise.

“That’s a completely different story Mick. Anyways, Mickey stole the gun and I had to go get it back. So I went to his house, went into his room, and we uh, we had a little fight.”

“It was a fuckin’ brawl. Which I won, by the way.”

Ian looked a Mickey and smiled. “I’d say we both won in the end.”

Mickey scratched his hair. “Well yeah, you could fuckin’ say that.”

Connor sat up. “So let me get this straight – you two fucked for the first time after a fight?”

Ian and Mickey both nodded their heads.

“Ugh that’s something I’d always wanted – like I like play-fighting-”

Oliver smiled and looked down at his plate. “Yeah you do-”

Connor side-eyed Oliver. “-Babe…but, uh, yeah, like an actual fight turning into sex was always one of my fantasies.”

“I’ll add that to the list.”

“That’s never gonna happen Ollie, I’d never want to actually fight with you.”

“’Cause you know you’d lose?”

“I dunno if I’d mind losing…”

Even though Mickey could feel his own eyebrows raised in his usual skeptical look, he also realized how nice it felt to finally be out with another couple of guy who, even though they were from different backgrounds than him and Ian, also had a lot in common with them. Mickey couldn’t remember hearing anyone but him and Ian talk about gay sex so freely.

“Connor, you ever think about investing in some ben wa beads?”

Connor turned to Mickey, apparently surprised that this South Side boy had a kinky side.

“Yeah, I might’ve once or twice.”

“Well lemme tell you man…”

* * *

 

The night had taken a decisive turn in that moment, and although at times the four men’s conversation had gotten loud enough to elicit stares from the other customers, they really didn’t care. Connor had come away knowing a lot more about sex toys than he had when he’d entered the restaurant, and he’d shared everything he could about how to give the perfect rimjob without actually demonstrating one on Oliver right then and there. Ian had taken out his phone and furiously typed up notes, determined to use this knowledge later.

As they were leaving, and Ian and Oliver were talking about some piece of work gossip or another, Connor slipped Mickey his card. “If anyone ever gives you shit at your job – anyone – just give me a call. I can do it pro bono, no problem.”

Mickey looked back at him. “I’m not a fuckin’ charity case.”

“Yeah, I know that man, but we can all use some help sometimes, trust me, I know that. And you’re definitely someone I’d be happy to lend a hand to if I could help you out at some point.”

Mickey raised his eyebrows. “What – like a friend or something?”

Connor smirked. “Maybe – I’ve got the feeling that a word like that is a pretty big step for both of us though.”

“You’re right about that.”

Connor offered his hand, and Mickey firmly grasped it.

“Nice meeting you, Connor Walsh.”

“Good to meet you too, Mickey-?”

“Milkovich.”

“Mickey Milkovich. Well I’m sure I’ll see you around – our puppies – err – boyfriends seem pretty eager to set up another date.”

Mickey snickered at the joke. “Yeah, I’ll see you around man.”

Once their boyfriends were done talking, they all exchanged goodbyes and headed out, taking the El in opposite directions.

Connor was full from the dinner, and closed his eyes as he rested against the window of the train.

“So, how’d you like them?”

Connor opened his eyes to see Oliver looking at him expectantly.

“They’re fine. It was a good choice on your part to set that up.”

Oliver leaned over and kissed Connor on the forehead. “Good thing I’m here to make the good choices.”

Connor lay down, curling up his legs and settling his head in Oliver’s lap. “Yeah, that’s for sure.”

* * *

 

Mickey leaned against Ian, his eyes closed as the train rocked him towards sleep.

“So? What’d you think?”

Mickey opened his eyes to see Ian looking at him with his puppy face.

“It turned out…better than I expected.”

“You’d be down to see them again?”

“Guess so. But that’s not the only thing I’m down for.”

“One out of ten Mick. Poor, poor exection.”

“Hey, I’m just tryin’ man.”

Ian kissed the top of Mickey’s head. “It’s cute when you try.”

Mickey curled up into a little ball and rested his head on Ian’s lap. “What about this? This cute enough for you?”

Ian petted Mickey’s slick black hair. “Better than anything I ever could have asked for.”


End file.
